STABLE WATER-IN-OIL EMULSIONS WITH SPREADABLE OILS

Description

[0001] The invention comprises a cosmetic and / or dermatological preparation based on a water-in-oil emulsion comprising at least two W / O emulsifiers and at least one oil with a spreading value greater than 600 mm² / 10 min.

[0002] Emulsions, particularly W / O, O / W, O / W / O, or W / O / W emulsions, are frequently used in cosmetic and medicinal preparations. Emulsions are generally understood to be heterogeneous systems consisting of two immiscible or only partially miscible liquids, which are usually referred to as phases. In an emulsion, one of the two liquids (W / O) is dispersed in the other liquid in the form of very fine droplets. The liquids (pure or as solutions) are present in an emulsion in a more or less fine distribution, which is generally only moderately stable.

[0003] If the two liquids are water and oil, and oil droplets are finely dispersed in the water, then it is an oil-in-water emulsion (O / W emulsion, e.g., milk). The fundamental properties, such as electrical conductivity, sensory properties, and the colorability of the continuous phase, of an O / W emulsion are determined by the water. A water-in-oil emulsion (W / O emulsion, e.g., butter) follows the reverse principle, with the fundamental properties here determined by the oil.

[0004] The state of the art identifies several key factors that have a positive influence on the stability and rheology of emulsions.

[0005] Emulsions generally require one or more emulsifiers, thickeners and / or consistency enhancers for their formation and stabilization in order to remain stable for a cosmetically acceptable period, generally 1 year after opening a cosmetic preparation.

[0006] Formulating free-flowing emulsions presents a particular challenge. Consumers highly value these emulsions for their excellent spreadability, but achieving a stable formulation is a technological challenge.

[0007] Ethoxylated emulsifiers are frequently used to stabilize emulsions. They are generally known to produce robust, stable emulsions and often cover a relatively broad sensory range. However, it is also known that ethoxylated emulsifiers act as penetration enhancers due to their PEG units.

[0008] EP 1 192 935 A2 discloses WO emulsions comprehensively including polyethers such as PEG-45 (dodecyl glycol) copolymer and PEG-22 (dodecyl glycol) copolymer.

[0009] The use of polyethylene glycols and / or polyethylene glycol derivatives and their derivatives is controversially discussed in public, as they are suspected of making the skin more permeable to foreign bodies such as pollutants after topical application.

[0010] Furthermore, under the influence of sunlight, the photounstable polyethylene glycol (PEG)-containing emulsifiers can decompose and trigger unpleasant skin reactions.

[0011] For the reasons mentioned above, consumers are increasingly seeking cosmetic formulations that are free of this class of substances.

[0012] PEG emulsifiers are currently most commonly used to develop water-in-oil (W / O) emulsions with appealing sensory properties. Since many consumers seek products free of this class of substances, stabilizing W / O emulsions without these substances while simultaneously achieving a pleasant skin feel presents a technological challenge.

[0013] Regarding stability, the challenge lies particularly in scaling up, and in terms of skin feel, parameters such as "fast and easy absorption, low stickiness" are difficult to achieve without PEG stabilizers.

[0014] It is therefore desirable to provide emulsion preparations without ethoxylated emulsifiers that are nevertheless as versatile as possible and, above all, stable.

[0015] Furthermore, cosmetic or dermatological preparations must meet certain aesthetic and sensory criteria in order to achieve sufficient consumer acceptance.

[0016] However, it is known that the addition of skin moisturizers often leads to the preparations appearing sticky.

[0017] It is known that the viscosity of water-in-oil (W / O) emulsions depends on the amount of emulsifier used. High concentrations result in creams with a high consistency, while reducing the concentration makes the systems flowable, often rendering them unstable, particularly during upscaling. Therefore, formulating flowable W / O emulsions currently presents a significant technological challenge.

[0018] WO 2009080657 A2 discloses W / O emulsions comprehensively in addition to hydrophobically modified polysaccharides, starches and / or agar polyglycerol-4 diisostearate polyhydroxystearate sebacate (Isolan GPS ®< ).

[0019] FR 2927535 discloses stable water-in-oil emulsions as cosmetic preparations comprising esters of fatty acids and polyols. Polyglycerol-4 diisostearate polyhydroxystearate sebacate (Isolan GPS®) is mentioned as a preferred ester. Glycerin is preferably chosen in the described preparations. The preparations should not be sticky on the skin.

[0020] WO 2008 / 055692 A2 comprehensively describes silicone-free skin protectants containing, among other things, oils and polyols as emulsifiers polyglycerol-4 diisostearate, polyhydroxystearate sebacate and / or polyglyceryl-2 dipolyhydroxystearate.

[0021] A crucial property of cosmetic products for consumers, yet difficult to quantify, is their texture and sensory properties. The term "texture" refers to those properties of a cosmetic product that stem from its structural composition, are perceived through touch, and can potentially be expressed in mechanical or rheological flow characteristics. Texture can be tested, in particular, using sensory methods. The texture of cosmetic products, which can be influenced by additives, is almost as important to consumers as their objectively measurable effects.

[0022] The term "sensory science" refers to the scientific discipline that deals with the evaluation of cosmetic preparations based on sensory impressions. The sensory assessment of a cosmetic product is based on visual, olfactory, and haptic impressions. Visual impressions: all characteristics perceptible to the eye (color, shape, structure). Olfactory impressions: all odor impressions perceptible when inhaling through the nose, which can often be differentiated into initial scent (top note), main scent (mid note, body), and after-scent (finish). Volatile substances released only during application also contribute to the olfactory impression. Haptic impressions: all sensations of touch, primarily relating to the texture and consistency of the product.

[0023] Sensory analysis utilizes the possibility of comprehensively capturing the overall sensory impression of a product. Disadvantages of sensory analysis include the subjectivity of the impression, the susceptibility of the test subjects to influence, and the resulting significant variability in the results. These weaknesses are addressed today through the use of groups of trained test subjects, mutual protection of the testers, and statistical evaluation of the often numerous analytical data points.

[0024] A further object of the present invention was therefore to provide preparations which, in addition to the criteria usual for cosmetics such as tolerability, shelf life, and the like, also offer consumers significant, previously unknown cosmetic, and in particular sensory, benefits. In particular, it was an aim to create a shelf-stable formulation that provides care without being slippery, oily, or greasy, and at the same time exhibits a clear "lotion-like" feel, i.e., flowable, and NOT a cream-like feel.

[0025] The invention is a cosmetic and / or dermatological preparation according to claim 1.

[0026] Diisostearoyl polyglyceryl-3 dimer dilinoleates are PEG-free emulsifiers and are known as Isolan® (PDI) and polyglyceryl-4 diisostearate / polyhydroxystearate / sebacate as Isolan® (GPS) from Evonik, with an HLB value of approximately 5.

[0027] Surprisingly, the use of these two W / O emulsifiers according to the invention in combination with the slightly spreading oil(s) has made it possible to solve the aforementioned technical challenges.

[0028] The use of a combination of two W / O emulsifiers in combination with one or more slightly spreading oils results in free-flowing, easily spreadable lotions with an appealing, i.e., non-oily, sensory experience.

[0029] The use of relatively high quantities of easily spreading oils surprisingly optimizes the sensory properties of the preparation according to the invention. Easily spreading oils are defined as oils with a spreading capacity greater than 600 (mm² / 10 min) and preferably a viscosity of less than 10 mPas. Isopropyl palmitate is particularly preferred.

[0030] In a comparative test, the viscosities of two W / O emulsion preparations were investigated, as shown in the following table. Viscosity in mPas Appearance and sensory experience Example recipe 4 5400 A fluid lotion with a pleasant skin feel, nourishing but not oily or greasy. Example formulation 4 without isopropyl palmitate but with 9.5% tri-isostearin 26 750 Rich cream, greasy and oily Spreadability of isopropyl palmitate: 625 (mm² / 10 min) Spreadability of Tri Isostearin: 310 (mm² / 10 min)

[0031] The W / O emulsion preparation without the oils according to the invention exhibited a viscosity of 26,750 mPas and was a rich cream. Only by replacing an oil with a low spreading value (tri isostearin) with an oil with a high spreading value (isopropyl palmitate) could the viscosity of the preparation be reduced to 5,400 mPas, resulting in a lotion with a pleasant skin feel.

[0032] It is surprising that simply changing one oil had such a fundamental impact on the viscosity of the preparation.

[0033] One or more oils with a spreading value greater than 600 mm² / 10 min are therefore surprisingly suitable for modifying, in particular reducing, the viscosity of the cosmetic water-in-oil emulsions they contain.

[0034] By replacing the oil phase with oils having a spreading value greater than 600 mm² / 10 min, preparations can be made that can be individually adapted to consumer wishes.

[0035] The aim of the invention was to create a shelf-stable formulation that provides care without being slippery, oily, or greasy. This has been achieved precisely with the formulation according to the invention. It has more structure and conveys this through its sensory impression. Consumers readily interpret this as "provides care without unpleasant side effects such as oiliness or greasyness."

[0036] A special feature is that the formulation is still free-flowing, meaning it can be used as a lotion. Lotion-like properties, i.e., free-flowing, are advantageous in formulations that have a viscosity greater than 4000 mPas and do not exhibit the sensory "cream" effect.

[0037] What's also surprising is that this doesn't come at the expense of shelf life. Cosmetics professionals now have a way to meet individual consumer demands for improved sensory properties without having to worry about compromising safety and stability.

[0038] Preferably, the preparations according to the invention do not include any additional emulsifiers. The proportion of additional emulsifiers should therefore preferably be below 0.01% by weight, based on the total mass of the preparation, in order to be considered to be according to the invention – without additional emulsifiers.

[0039] Similarly, according to the invention, the addition of polyethylene glycols and / or polyethylene glycol derivatives can be omitted. The proportion of PEGs is therefore less than 1 wt.%, in particular 0 wt.%, based on the total mass of the preparation.

[0040] The oil content of the preparations according to the invention is advantageously in the range of 10 to 30 wt.%, preferably between 15 to 25 wt.%, particularly preferably in the range of 18 to 22 wt.%, based on the total mass of the preparation.

[0041] According to the invention, the lipid phase comprises at least one oil with a spreading value greater than 600 (mm² / 10 min). It is preferred if a second oil with a spreading value greater than 600 (mm² / 10 min), preferably greater than 800 mm² / 10 min, and particularly preferably greater than 1000 mm² / 10 min, is also included.

[0042] According to the invention, one or more of the oils listed in Table 1 below with a spreading value above 600 mm² / 10 min and a viscosity of less than 10 mPas are to be selected. Table 1: Oils with a spreading value greater than 600 mm² / 10 min INCI Viscosity [mPas] Spreadability (20 µl / red band filter) [mm² / 10 min] Isopropyl Palmitate 6,2 625 Isopropyl Myristate 4,6 707 Coco-Caprylate / Caprate 5 755 Isopropyl Isostearate 9,5 790 Cyclomethicone 4-5 804 - 845 Butylene Glycol Dicaprylate / Dicaprate 9,6 813 Dicaprylyl Carbonate 6,3 875 Isopropyl Stearate 6,8 910 Ethylhexyl Cocoate 7,9 930 Dibutyl Adipate 5 935 Isodecyl Neopentanoate 3,8 962 Isohexadecane 3,7 990 C13-16 Isoparaffin 2,6 1018 Dicaprylyl Ether 3,3 1020

[0043] Isopropyl palmitate with a spreading value of approximately 625 mm² / 10 min and C13-16 isoparaffin with a spreading value of approximately 1018 mm² / 10 min are preferred oils.

[0044] With respect to the total mass of the oil phase, the proportion of oils with a spreading value greater than 600 mm² / 10 min is advantageously 30 to 90 wt.%, preferably 40 to 80 wt.%, particularly preferably 40 to 60 wt.%, based on the total mass of the oil phase.

[0045] Surprisingly, the use of easily spreadable oils made it possible to formulate stable, free-flowing (at RT) WO emulsions.

[0046] Preferably, preparations based on a water-in-oil emulsion comprise an oil with a spreading value greater than 600 mm² / 10 min and an oil with a spreading value greater than 800 mm² / 10 min; it is particularly advantageous if the second spreading oil has a spreading value greater than 1000 mm² / 10 min.

[0047] Advantageous were oils with a spreading value greater than 600 mm² / 10 min and a viscosity less than 10 mPas, particularly advantageous with a spreading value between 1020 and 600, namely isopropyl palmitate and / or C13-16 isoparaffin.

[0048] At room temperature, isopropyl palmitate has a viscosity of 6.2 mPas, measured using a viscotester VT-02, manufactured by Haake, at 25°C using the rotating body 1 or 2 and reading the scale 1 or 2, corresponding to a shear rate of 10 Pa / s.

[0049] In cosmetics, the ability of an oil to spread easily or minimally on the skin is referred to as spreadability. The higher the spreadability of an oil, the more easily it spreads on human skin.

[0050] The spreading value (in mm² / 10 min) is measured using the following procedure: 20 µl of the substance to be tested are dropped onto the center of a red band filter paper from Schleicher & Schüll. A stopwatch is started immediately, and after 10 minutes, the area wetted by the substance during this time is measured.

[0051] The measurement is carried out in a room with a constant temperature of 25°C + / - 1°C.

[0052] Hydrophilic stabilizers such as thickeners and fatty alcohols may optionally be included according to the invention.

[0053] The preparations according to the invention advantageously comprise at least one skin moisturizing agent in a proportion of 5 to 20 wt.%, based on the total mass of the preparation. A glycerin content of 7 to 15 wt.% is preferred, and 10 wt.% is particularly preferred.

[0054] By using the emulsifier combination according to the invention, it has been possible to formulate a water-in-oil (W / O) emulsion that, despite high amounts of skin moisturizing agents such as glycerin, has a very pleasant skin feel and is also stable under stress tests such as storage at elevated or fluctuating temperatures. This stability is not only present in the 1 to 5 kg batches produced on a laboratory scale, but also in larger quantities such as 100 to 500 kg and even in production on a ton scale. This process, known as "up-scaling," is known to be particularly sensitive for conventional W / O emulsions. For the preparations according to the invention, the up-scaling process proved to be surprisingly straightforward.

[0055] Emulsifiers enable two immiscible liquids (for example, oil and water) to mix and form an emulsion. Due to their amphiphilic nature, their fat-soluble part penetrates the oil. The hydrophilic part then disperses the resulting oil droplets in the aqueous environment. Emulsifiers do not primarily possess detergent or surfactant properties.

[0056] Emulsifiers reduce the interfacial tension between the two phases and, in addition to reducing the work required at the interfaces, also stabilize the emulsion. They stabilize the emulsion through interfacial films and by forming steric or electrical barriers, thus preventing the coalescence of the emulsified particles.

[0057] For compounds to be effective as emulsifiers, they must possess a specific molecular structure. A structural characteristic of such compounds is their amphiphilic molecular structure. The molecule of such a compound has at least one group with an affinity for substances of high polarity (polar group) and at least one group with an affinity for nonpolar substances (nonpolar group).

[0058] A distinction is made between non-ionic, anionic and cationic emulsifiers.

[0059] A characteristic of the hydrophilicity of a given emulsifier is its HLB value, which is calculated using the following formula: HLB = 20 x (1- M lipophil / M), where M lipophil represents the molar mass of the lipophilic component in the emulsifier and M represents the molar mass of the entire emulsifier.

[0060] Generally, emulsifiers with an HLB value up to approximately 8 are considered W / O emulsifiers. O / W emulsifiers, on the other hand, have HLB values ​​greater than 8 up to 15. Substances with HLB values ​​greater than 15 are often referred to as solubilizers.

[0061] According to the invention, it has now been found that by selecting two water-in-oil (W / O) emulsifiers, preferably present in the preparation at a proportion of more than 1.5% by weight, and additionally including at least one easily spreading oil, free-flowing lotions are obtained that are characterized by a nourishing yet non-oily and non-greasy sensory experience (see example formulations). These formulations are also stable over a long period, surprisingly even when stored at different or fluctuating temperatures. It is known that the production of larger quantities of such formulations often presents problems with upscaling. This process, known as "upscaling," is known to be particularly sensitive for conventional W / O emulsions. For the preparations presented within the scope of this invention, the upscaling process proved to be surprisingly trouble-free, which is due to the selection of emulsifiers according to the invention.

[0062] The invention preferably relates to a cosmetic or dermatological preparation based on a water-in-oil emulsion which contains no (0%) ethoxylated emulsifiers, polyethylene glycols and / or polyethylene glycol derivatives.

[0063] Furthermore, the preparations according to the invention advantageously comprise one or more powdered raw materials, which are preferably present in a proportion of up to 5 wt.%, preferably 0.2 to 2 wt.%, based on the total mass of the preparation. Preferred powdered raw materials are aluminum starch octenylsuccinate and / or talc.

[0064] The cosmetic or dermatological preparations according to the invention may further contain cosmetic excipients and other active ingredients such as are commonly used in such preparations, e.g.Preservatives, preservative aids, bactericides, antifoaming agents, dyes and pigments, thickeners, moisturizing and / or humectant substances, fats, oils, waxes or other common components of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives, self-tanning agents, buffers, pH regulators, plant extracts, surfactants, propellants, powders, sebum-absorbing substances, UV filters, active ingredients such as anti-aging, anti-cellulite, anti-acne, anti-rosacea, anti-eczema, antioxidants, moisturizers, chelating agents, antiperspirants, bleaching agents and dyes, etc., provided that the addition does not impede the required properties with regard to PEG-free status, emulsifier content, required stability and sensory properties.

[0065] The water content of the preparations according to the invention is advantageously between 40 and 80 wt.%, preferably between 50 wt.% and 70 wt.%, particularly preferably between 55 wt.% and 65 wt.%, in each case based on the total mass of the preparations.

[0066] The following examples illustrate the preparations according to the invention. Unless otherwise stated, the numerical data refer to the weight percentages in relation to the total mass of the preparation. Example 1:

[0067] 0.5% Polyglyceryl-4 Diisostearate / Polyhydroxystearate / Sebacate 1.9% Diisostearoyl Polyglyceryl-3 Dimer Dilinoleate 3% Cera Microcristallina 10% Isopropyl Myristate 10% Dicapylyl Ether 1% Talc 12% Glycerin 1% Propylene Glycol 0.1% Hexanediol 0.15% Potassium Sorbate 0.1% Citric Acid 0.2% Sodium Citrate 0.4% Perfume With Aqua ad 100% Example 2:

[0068] 0,8 % Polyglyceryl-4 Diisostearate / Polyhydroxystearate / Sebacate 1,9 % Diisostearoyl Polyglyceryl-3 Dimer Dilinoleate 2,5 % Cetylpalmitate 0,1% Cera Microcristallina 2% C13-16 Isoparaffin 2% Cyclomethicone 4% Argania Spinosa Kernel Oil 0,1% Calendula Oil 6,5% Paraffinum Liquidum 6,5% Isopropyl Palmitate 10% Glycerin 2% Tapoca Starch 0,15% Potassium Sorbate 0,2% Sodium Citrate 0,1% Citric Acid 0,15% Parfüm Mit Aqua ad 100% Example 3:

[0069] 1,5 % Polyglyceryl-4 Diisostearate / Polyhydroxystearate / Sebacate 1,5 % Diisostearoyl Polyglyceryl-3 Dimer Dilinoleate 2,7% Shea Butter 7,5% Isohexadecane 5, 3% Dibutyl Adipate 6,5% Paraffinum Liquidum 0,1% Sonnenblumenöl 13,75% Glycerin 0,5% Ethylhexylglycerin 1% Aluminium Starch Octenylsuccinate 1% Nylon-12 0,15% Potassium Sorbate 0,2% Sodium Citrate 0,1% Citric Acid 0,3% Parfüm Mit Aqua ad 100% Example 4:

[0070] 0,8 % Polyglyceryl-4 Diisostearate / Polyhydroxystearate / Sebacate 1,4 % Diisostearoyl Polyglyceryl-3 Dimer Dilinoleate 1 % Cera Microcristallina + Paraffinum Liquidum 0,5 % Cera Microcristallina 2 % Paraffinum Liquidum 1% Prunus Amygdalus Dulcis Oil 0,5% Cetyl Palmitate 9,5% Isopropylpalmitate 6% C13-16 Isoparaffin 0,5% Aluminium Starch Octenylsuccinate 10% Glycerin 0,15% Potassium Sorbate 0,7 Magnesium Sulfate 0,1% Maris Sal 0,5% Glyceryl Glucoside 0,2% Sodium Citrate 0,1% Citric Acid 0,35% Parfüm Mit Aqua ad 100% Example 5:

[0071] 1,4 % Polyglyceryl-4 Diisostearate / Polyhydroxystearate / Sebacate 0,8 % Diisostearoyl Polyglyceryl-3 Dimer Dilinoleate 0,2 % Cera Microcristallina 1% Shea Butter 2,5% Cera Microcristallina + Paraffinum Liquidum 7,5% Caprylic / Capric Triglyceride 12 % Dicaprylyl Ether 0,1% Olivenöl 1% Talkum 0,2% Aluminium Starch Octenylsuccinate 12% Glycerin 0,1% Caprylyl Glycol 0,15% Potassium Sorbate 0,1% Citric Acid 0,2% Sodium Citrate 0,4% Parfüm Mit Aqua ad 100% Example 6:

[0072] 1,1 % Polyglyceryl-4 Diisostearate / Polyhydroxystearate / Sebacate 1,2 % Diisostearoyl Polyglyceryl-3 Dimer Dilinoleate 0,2 % Cera Microcristallina 1% Shea Butter 2,5% Cera Microcristallina + Paraffinum Liquidum 7,5% C13-16 Isoparaffin 12 % Dicaprylyl Ether 0,1% Olivenöl 1% Talkum 0,2% Aluminium Starch Octenylsuccinate 12% Glycerin 0,1% Caprylyl Glycol 0,15% Potassium Sorbate 0,1% Citric Acid 0,2% Sodium Citrate 0,4% Parfüm Mit Aqua ad 100%

Claims

1. Cosmetic and / or dermatological preparation based on a water-in-oil emulsion comprising only two W / O emulsifiers, wherein diisostearoyl polyglyceryl-3 dimer dilinoleate and polyglyceryl-4 diisostearate / polyhydroxystearate / sebacate are selected as W / O emulsifiers, and at least one oil with a spreadability value greater than 600 mm2 / 10 min, wherein the fraction of oils with a spreadability value greater than 600 mm2 / 10 min is selected in the range of 10% to 20% by weight, based on the total mass of the preparation, and wherein the oils with a spreadability value greater than 600 mm2 / 10 min are selected from the group of isopropyl palmitate, isopropyl myristate, coco-caprylate / caprate, isopropyl isostearate, cyclomethicone, butylene glycol dicaprylate / dicaprate, dicaprylyl carbonate, isopropyl stearate, ethylhexyl cocoate, dibutyl adipate, isodecyl neopentanoate, isohexadecane, C13-16 isoparaffin and / or dicaprylyl ether, and wherein wherein to measure the spreadability value (in mm2 / 10 min), 20 ml of the substance to be examined are applied dropwise centrally to a red band filter paper from Schleicher & Schüll, a stopwatch is immediately started and, after 10 minutes, the area which has been wetted by the substance in this time is measured, the measurement being carried out in a temperature-constant space at 25°C + / - 1°C.

2. Preparation according to Claim 1, characterized in that the oils with a spreadability value greater than 600 mm2 / 10 min have a viscosity of 10 mPas and less.

3. Preparation according to either of the preceding claims, characterized in that the oils with a spreadability value greater than 600 mm2 / 10 min are selected from the group of isopropyl palmitate and C13-16 isoparaffin.

4. Preparation according to any of the preceding claims, characterized in that an oil with a spreadability value greater than 600 mm2 / 10 min and at least one oil with a spreadability value greater than 1000 mm2 / 10 min are included.

5. Preparation according to any of the preceding claims, comprising at least one skin moisturizer in a fraction of in total 5% to 20% by weight, based on the total mass of the preparation.

6. Preparation according to Claim 5, characterized in that a skin moisturizer selected is glycerol.

7. Preparation according to any of the preceding claims, characterized in that one or more powder raw materials are included.

8. Preparation according to Claim 7, characterized in that the fraction of powder raw materials is up to 5% by weight, in particular 0.2% to 2% by weight, based on the total mass of the preparation.

9. Preparation according to Claim 7 or 8, characterized in that a powder raw material selected is aluminium starch octenylsuccinate and / or talc.

10. Preparation according to any of the preceding claims, characterized in that the water fraction is selected in the range from 40% to 80% by weight, in particular between 55% and 65% by weight, based on the total mass of the preparation.

11. Preparation according to any of the preceding claims, characterized in that the fraction of polyethylene glycols and / or polyethylene glycol derivatives is less than 1% by weight, in particular 0% by weight, based on the total mass of the preparation.